Recent Advances in Heterohelicene-Based Circularly Polarized Luminescence Materials

doi:10.6023/cjoc202504012

Abstract

Heterohelicenes represent a class of polycyclic aromatic hydrocarbons (PAHs) with helically chiral structures, and in recent years these compounds and their derivatives have emerged as a research focus in the field of chiral luminescent materials due to their unique optical properties and circularly polarized luminescence (CPL). This review comprehensively summarizes the modulation mechanisms by which the incorporation of main-group elements (e.g., N, O, S) regulates the electronic structures, luminescence performance, and chiroptical properties of helicenes. The recent advances in the design of CPL materials based on heterohelicenes that are doped with N, O, S or B/N, O/N, S/N is introduced in detail, and their potential applications in 3D displays, information encryption, and bioimaging are prospected. Therefore, studies on the synthesis, structural design, and photophysical properties of heterohelicene-based CPL-active molecules hold significant importance in advances of optoelectronics and materials science.

Key words: helicenes, circularly polarized luminescence, heteroatom doping, structure-property relationship, review

Cite this article

Cuiping Sun, Yuting Xue, Pangkuan Chen. Recent Advances in Heterohelicene-Based Circularly Polarized Luminescence Materials[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4048-4069.

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Fig. & Tab. 28

Figure 1. (a) Structures of C; (b) CPL spectra of C both in CH2Cl2 and in the film state (inset: photographs under 365 nm UV lamp); (c) Chemical oxidations of (P,P)-C (c=5×10－3 mol/L, CH2Cl2/CH3CN) with different amounts of NOSbF6 monitored by UV-Vis-NIR absorption spectra (inset: photographs of solutions after addition of NOSbF6)[20]

Figure 2. (a) Structures of N7-BMes2 and N7-TTM; (b) UV-vis absorption (solid lines) and emission (dashed lines, λex=377 nm) spectra of N7-BMes2 and N7-TTM in n-hexane (c=1.0×10－5 mol/L); (c, d) CPL spectra of enantiomers for N7-BMes2 (in CH2Cl2) and N7-TTM (in n-hexane)[21]

Figure 3. (a) Structures of the electron-rich macrocycles 1 and 2; (b) Circularly polarized luminescence spectra (1.0×10－5 mol/L) in CH2Cl2 at 298 K of 1 and 2; (c) Chemical oxidations of 1 (c=5×10－5 mol/L, CH2Cl2/CH3CN) with different amounts of NOSbF6 monitored by UV-vis-NIR absorption spectra (inset: photographs of solutions after the addition of NOSbF6; (d) in situ UV/Vis-NIR spectra monitored by spectroelectrochemical measurements in CH2Cl2 upon the oxidation of 1 at increased scan potentials (0~2.5 V)[22]

Figure 4. (a) Structure of the double aza[7]helicene 3; (b) Structure of the negatively curved aza-NG 4; (c) CD and CPL spectra for 3 in dichloromethane (c=1.0×10－5 mol/L) at 298 K[26]

Figure 5. (a) Structures of the N-doped helical nonalternant nanographenes CPH-1~CPH-3; (b) CD spectra and |gabs| curves and (c) CPL emission spectra and glum curves of CPH-2 and CPH-3 measured in dichloromethane (1×10－5 mol/L) at 298 K[30]

Figure 6. (a) Structures of compounds 5, 6a, 6b and 6b-H2; (b~d) CD (full line) and CPL (dashed line) spectra of 5, 6b and 6b-H2 in dichloromethane at 298 K[31]

Figure 7. (a) Structures of compounds 7~10; (b) CD, (c) UV/Vis, (d) CPL, and (e) FL spectra in CH2Cl2 (inset: photographs of dichloromethane solutions of each (P)-helicene under black light (λ=365 nm) are shown)[32]

Figure 8. (a) Structures of compounds 11~14; (b) CD and CPL spectra of 11~13 in dichloromethane[33]

Figure 9. (a) Structures of compounds NHn (n=1~5); (b) CD and CPL spectra of NH2, NH3 and NH4[37]

Figure 10. (a) Structures of compounds [n]AH-Bum [m=(n－1)/2], [9]AH, 15, 15-Et and 15-Bu; (b) CD and CPL spectra of [9]AH-Bu4 (black), [11]AH-Bu5 (red), [13]AH-Bu6 (blue), and [15]AH-Bu6 (green) in THF at room temperature; (c) CD and CPL spectra of 15-Et and 15-Bu[41-42]

Figure 11. (a) Structure of the compound 16; (b) CD spectra of compound 16 and simulated spectrum of (M)-16 (black dash line); (c) CPL spectra of compound 16[45]

Figure 12. (a) Structures of compounds 17 and 18; (b) UV-vis (bottom) and CD (top) spectra of 17 and 18 in dichloromethane; (c) Fluorescence (bottom) and CPL (top) spectra of 17 and 18 in dichloromethane (1.0×10－5 mol/L)[46]

Figure 13. (a) Structures of compounds TB[n]H (n=5~8); (b) CD and CPL spectra of TB[7]H in 2-MeTHF[47]

Figure 14. (a) Structures of compounds TS[7]H, TT[7]H, TH[7]H; (b) CD (c=6.1×10－5 mol/L) and CPL (c=1×10－3 mol/L) spectra of TS[7]H, TT[7]H-2, and TH[7]H in dichloromethane[48]

Figure 15. (a) Structures of the compound 19; (b) CD and (c) CPL spectra of 19 in CH2Cl2 (c=1.0×10－5 mol/L)[49]

Figure 16. (a) Structures of compounds DO7H, DT7H, DS7H; (b) Structures of compounds DTH1, DTH2; (c~d) CD and CPL spectra of DO7H, DT7H, DS7H, DTH1, DTH2 in dichloromethane (c=1.0×10－5 mol/L)[53-54]

Figure 17. (a) Structure of the compound 20; (b) CD and CPL spectra of the compound 20 (The red dotted line shows the CD spectrum for (P,P,P)-20 simulated by TD-DFT at the B3LYP/6-311G (d, p) level)[55]

Figure 18. (a) Structures of compounds 21~23; (b) CD spectra of 21~23 in dichloromethane; (c) CPL spectra of 21~23 in dichloromethane[56]

Figure 19. (a) Structures of compounds A, A'; (b) CD and CPL spectra of compounds A, A'[58]

Figure 20. (a) Structures of compounds 24, 25, 2-C1, 2-C2, 3-C2; (b) CD and CPL spectra of compounds 24, 25 in dichloromethane; (c) CD and CPL spectra of compounds 2-C1, 2-C2, 3-C2[62-63]

Figure 21. (a) Structures of the compound BN[9]H; (b) CD and CPL spectra, corresponding gabs and glum values of the compound BN[9]H in toluene[65]

Figure 22. (a) Structures of compounds [8]HAB, [10]HAB, E[10]HAB-A, E[10]HAB-B and E[10]HAB-C; (b) CD and CPL spectra of compounds [8]HAB and [10]HAB in dichloromethane; (c) CD and (d) CPL spectra of E[10]HAB-A, E[10]HAB-B and E[10]HAB-C in dichloromethane[67-68]

Figure 23. (a) Structures of the compound 2B and fluoride adduct; (b) CD and CPL spectra of the compound 2B[72]

Figure 24. (a) Structures of compounds BN-HC, BiBN-HC and BiBN-BiHC; (b) CD and (c) CPL spectra of BN-heterocycle-fused helicenes in toluene (c=3.0×10－5 mol/L)[73]

Figure 25. (a) Structure of the compound H1-Me4; (b) CD and (c) CPL spectra of H1-Me4[74]

Figure 26. (a) Structures of compounds 26 and 27; (b) CD and CPL spectra of 27[75]

Figure 27. (a) Structures of compounds SNSN-S and (SNSN-S)2; CD spectra of (b) SNSN-S and (c) (SNSN-S)2 in THF; (d) CPL spectra of SNSN-S in THF[76]

Compound	Φ_F	g_abs/10^－3	g_lum/10^－3	Compound	Φ_F	g_abs/10^－3	g_lum/10^－3
C	0.86	0.48	0.22	19	0.48	7.5	0.59
rac-N7-Bmes2	0.32	4.17	3.39	DO7H	0.71	10	0.75
rac-N7-TTM	0.5	2.7	3.57	DT7H	0.43	14	1.2
1	0.26	33	1.5	DSTH	0.31	7.2	1.1
2	0.99	14	5	DTH1	0.83	4	2.2
3	0.45	—	2.4	DTH2	0.91	5.3	2.1
CPH-3	0.32	10	7	20	0.04	6.1	1.8
5	0.47	3.5	0.94	21	0.53	4.6	0.5
6a	0.01	2.5	—	22	0.26	4	1.6
6b	0.12	1.9	1.6	23	0.1	3.6	2.1
7	0.44	4.7	2.3	A	3.1	—	1.58
8	0.32	3.9	1.9	A'	3.5	—	4.3
9	0.61	2.1	0.74	2B	—	1.6	0.47
10	0.54	2.5	1.3	2B·F	—	3	1.7
11	0.1	4.7	3.5	BN-HC	0.11	0.6	—
12	0.22	3.7	2.4	BiBH-HC	0.2	2.19	1.95
13	—	2.8	—	BiBH-BiHC	0.87	2.15	2.06
14	—	—	—	24	0.72	1.7	1.5
9AH-Bu₄	0.16	5.6	4.5	25	0.85	1.3	1.1
11AH-Bu₅	0.16	4.2	4.2	2-C₁	0.85	1	0.75
13AH-Bu₆	0.09	4.2	1.7	2-C₂	0.81	2.7	1.9
15AH-Bu₆	0.07	1.7	5.7	3-C₂	0.59	4.1	2.3
15	0.07	—	—	BN[9]H	0.98	—	5.8
16-Et	0.35	2.4	1	[8]HAB	0.31	36	24
16-Bu	0.35	2.3	1	[10]HAB	0.24	61	48
16	0.4	2.98	4.3	E[10]HAB-A	0.82	24	17
17	0.2	—	4.6	E[10]HAB-B	0.67	11	11
18	3.5	—	12.5	E[10]HAB-C	0.72	12	8
TB[7]H	0.19	3	15	H1-M4	0.17	3.3	3.5
TS[7]H	—	1	—	SNSN-S	—	—	1.2

Table 1. Luminescence quantum efficiency (ΦF), absorption asymmetry factor (gabs) and luminescence asymmetry factor (glum) of all compounds

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杂螺烯圆偏振发光材料的研究进展